Double Silylation of 1,4-Bis(trimethylsilyl)butadiyne with Disilanes Using a Palladium Catalyst

Article abstract of DOI:10.1246/bcsj.63.3103

Reaction of 1,4-bis(trimethylsilyl)butadiyne with polychlorodisilanes Si2Cl_xMe_6-x in the presence of a palladium catalyst gives, after methylation, 1,1,4,4-tetrakis(trimethylsilyl)butatriene and/or 1,1,2,4-tetrakis(trimethylsilyl)-1-buten-3-yne selectively.Hydrogenation, hydrosilylation, and oxidation of the obtained butatriene were found to take place at C(1)=C(2) double bond exclusively.The regioselectivity is ascribed to the geminally substituted silyl groups which sterically direct the attack of electrophile and stabilize postulated radical intermediates.